Literature DB >> 21913732

Bioinspired synthesis of hirsutellones A, B, and C.

K C Nicolaou1, Ya-Ping Sun, David Sarlah, Weiqiang Zhan, T Robert Wu.   

Abstract

The total synthesis of hirsutellones A (1), B (2), and C (3) has been achieved through a bioinspired late-stage sequence starting from advanced intermediate 6. The sequence proceeded via labile intermediate 17,1'-dehydrohirsutellone B (5) and delivered, in addition to the natural products (1-3), hirsutellone analogue 1',2',17-epi-hirsutellone C (1',2',17-epi-3).
© 2011 American Chemical Society

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Year:  2011        PMID： 21913732      PMCID： PMC3207260          DOI： 10.1021/ol202239u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Construction of the cyclophane core of the hirsutellones via a RCM strategy.

Authors:  Mingzheng Huang; Liqiang Song; Bo Liu
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

2.  Hirsutellone F, a dimer of antitubercular alkaloids from the seed fungus Trichoderma species BCC 7579.

Authors:  Masahiko Isaka; Wai Prathumpai; Patcharaporn Wongsa; Morakot Tanticharoen
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  Stereoselective Synthesis of the Decahydrofluorene Core of the Hirsutellones.

Authors:  Geoff T Halvorsen; William R Roush
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

4.  Biosynthesis of structurally unique fungal metabolite GKK1032A(2): indication of novel carbocyclic formation mechanism in polyketide biosynthesis.

Authors:  Hideaki Oikawa
Journal:  J Org Chem       Date:  2003-05-02       Impact factor: 4.354

5.  Total synthesis of hirsutellone B.

Authors:  K C Nicolaou; David Sarlah; T Robert Wu; Weiqiang Zhan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

Authors:  S David Tilley; Keith P Reber; Erik J Sorensen
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005
  6 in total
  9 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 2.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649

3.  Xenoacremones D-H, Bioactive Tyrosine-decahydrofluorene Analogues from the Plant-Derived Fungus Xenoacremonium sinensis.

Authors:  Zhiguo Liu; Li Liu; Anqi Wang; Li Li; Sinan Zhao; Yanan Wang; Yi Sun
Journal:  Mar Drugs       Date:  2022-05-31       Impact factor: 6.085

4.  Total synthesis of myceliothermophins C, D, and E.

Authors:  K C Nicolaou; Lei Shi; Min Lu; Manas R Pattanayak; Akshay A Shah; Heraklidia A Ioannidou; Manjunath Lamani
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-27       Impact factor: 15.336

5.  Toward a synthesis of hirsutellone B by the concept of double cyclization.

Authors:  Keith P Reber; S David Tilley; Cheryl A Carson; Erik J Sorensen
Journal:  J Org Chem       Date:  2013-09-23       Impact factor: 4.354

6.  Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Authors:  Junjia Liu; T Aaron Bedell; Julian G West; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-01-28       Impact factor: 2.457

7.  Tricarbocyclic core formation of tyrosine-decahydrofluorenes implies a three-enzyme cascade with XenF-mediated sigmatropic rearrangement as a prerequisite.

Authors:  Zhiguo Liu; Wei Li; Peng Zhang; Jie Fan; Fangbo Zhang; Caixia Wang; Shuming Li; Yi Sun; Shilin Chen; Wenbing Yin
Journal:  Acta Pharm Sin B       Date:  2021-03-26       Impact factor: 11.413

8.  Bioactive PKS-NRPS Alkaloids from the Plant-Derived Endophytic Fungus Xylaria arbuscula.

Authors:  Ya Wang; Sinan Zhao; Tao Guo; Li Li; Tantan Li; Anqi Wang; Dandan Zhang; Yanlei Wang; Yi Sun
Journal:  Molecules       Date:  2021-12-27       Impact factor: 4.411

Review 9.  Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors:  Xufen Yu; Dianqing Sun
Journal:  Molecules       Date:  2013-05-24       Impact factor: 4.411
  9 in total

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